DE10225927A1 - Verfahren zur Herstellung von Butandiol durch kombinierte Gasphasen- und Flüssigphasensynthese - Google Patents

Verfahren zur Herstellung von Butandiol durch kombinierte Gasphasen- und Flüssigphasensynthese

Info

Publication number: DE10225927A1
Authority: DE; Germany
Prior art keywords: hydrogenation; catalyst; reactor; stage; weight
Prior art date: 2002-06-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE10225927A

Other languages

German (de)

English (en)

Inventor

Michael Hesse

Stephan Schlitter

Holger Borchert

Markus Schubert

Markus Roesch

Nils Bottke

Rolf-Hartmuth Fischer

Alexander Weck

Gunther Windecker

Gunnar Heydrich

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-06-11

Filing date

2002-06-11

Publication date

2003-12-24

2002-06-11 Application filed by BASF SE filed Critical BASF SE

2002-06-11 Priority to DE10225927A priority Critical patent/DE10225927A1/de

2003-06-10 Priority to KR1020047020104A priority patent/KR100898455B1/ko

2003-06-10 Priority to AU2003274707A priority patent/AU2003274707A1/en

2003-06-10 Priority to PCT/EP2003/006057 priority patent/WO2003104176A1/de

2003-06-10 Priority to JP2004511246A priority patent/JP2005534658A/ja

2003-06-10 Priority to CNB038133504A priority patent/CN1294110C/zh

2003-06-10 Priority to EP03740211A priority patent/EP1515935A1/de

2003-06-10 Priority to US10/516,923 priority patent/US7169958B2/en

2003-12-24 Publication of DE10225927A1 publication Critical patent/DE10225927A1/de

Status Withdrawn legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 75
230000008569 process Effects 0.000 title claims abstract description 42
239000012071 phase Substances 0.000 title claims abstract description 20
239000007791 liquid phase Substances 0.000 title claims abstract description 19
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 title description 69
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238000003786 synthesis reaction Methods 0.000 title 1
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YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims abstract description 88
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QQVHEQUEHCEAKS-UHFFFAOYSA-N diundecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCC QQVHEQUEHCEAKS-UHFFFAOYSA-N 0.000 claims description 2
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UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims 1
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239000011651 chromium Substances 0.000 description 30
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JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 8
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QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
GXDVEXJTVGRLNW-UHFFFAOYSA-N [Cr].[Cu] Chemical compound [Cr].[Cu] GXDVEXJTVGRLNW-UHFFFAOYSA-N 0.000 description 1
PURJYVIHCDBIRA-UHFFFAOYSA-N [Cu]=O.[O-2].[Al+3].[O-2].[O-2].[Al+3] Chemical compound [Cu]=O.[O-2].[Al+3].[O-2].[O-2].[Al+3] PURJYVIHCDBIRA-UHFFFAOYSA-N 0.000 description 1
150000001257 actinium Chemical class 0.000 description 1
239000011149 active material Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229910052728 basic metal Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000004568 cement Substances 0.000 description 1
RNCXCPUOPDATPU-UHFFFAOYSA-N chromium(3+) oxocopper oxygen(2-) Chemical compound [O-2].[Cr+3].[Cu]=O.[O-2].[O-2].[Cr+3] RNCXCPUOPDATPU-UHFFFAOYSA-N 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229910000428 cobalt oxide Inorganic materials 0.000 description 1
IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
WCCJDBZJUYKDBF-UHFFFAOYSA-N copper silicon Chemical compound [Si].[Cu] WCCJDBZJUYKDBF-UHFFFAOYSA-N 0.000 description 1
VODBHXZOIQDDST-UHFFFAOYSA-N copper zinc oxygen(2-) Chemical compound [O--].[O--].[Cu++].[Zn++] VODBHXZOIQDDST-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
238000007599 discharging Methods 0.000 description 1
230000005611 electricity Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000010574 gas phase reaction Methods 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000009434 installation Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
229910052746 lanthanum Inorganic materials 0.000 description 1
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
229910052745 lead Inorganic materials 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
239000003863 metallic catalyst Substances 0.000 description 1
229910000476 molybdenum oxide Inorganic materials 0.000 description 1
CXJOEMLCEGZVPL-UHFFFAOYSA-N monoisopropyl phthalate Chemical compound CC(C)OC(=O)C1=CC=CC=C1C(O)=O CXJOEMLCEGZVPL-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000012856 packing Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000009419 refurbishment Methods 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
238000007740 vapor deposition Methods 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DE10225927A 2002-06-11 2002-06-11 Verfahren zur Herstellung von Butandiol durch kombinierte Gasphasen- und Flüssigphasensynthese Withdrawn DE10225927A1 (de)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
DE10225927A DE10225927A1 (de)	2002-06-11	2002-06-11	Verfahren zur Herstellung von Butandiol durch kombinierte Gasphasen- und Flüssigphasensynthese
KR1020047020104A KR100898455B1 (ko)	2002-06-11	2003-06-10	결합된 기상 및 액상 수소화에 의한 1,4-부탄디올의 제조방법
AU2003274707A AU2003274707A1 (en)	2002-06-11	2003-06-10	Method for the production of 1,4- butane-diol by combined gas-phase and liquid-phase hydrogenation
PCT/EP2003/006057 WO2003104176A1 (de)	2002-06-11	2003-06-10	Verfahren zur herstellung von 1,4- butandiol durch kombinierte gasphasen- und flüssigphasenhydrierung
JP2004511246A JP2005534658A (ja)	2002-06-11	2003-06-10	組み合わされた気相水素化及び液相水素化による１，４−ブタンジオールの製造方法
CNB038133504A CN1294110C (zh)	2002-06-11	2003-06-10	通过结合气相和液相氢化制备1,4－丁二醇的方法
EP03740211A EP1515935A1 (de)	2002-06-11	2003-06-10	Verfahren zur herstellung von 1,4-butandiol durch kombinierte gasphasen- und flüssigphasenhydrierung
US10/516,923 US7169958B2 (en)	2002-06-11	2003-06-10	Method for the production of 1,4- butane-diol by combined gas-phase and liquid-phase hydrogenation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10225927A DE10225927A1 (de)	2002-06-11	2002-06-11	Verfahren zur Herstellung von Butandiol durch kombinierte Gasphasen- und Flüssigphasensynthese

Publications (1)

Publication Number	Publication Date
DE10225927A1 true DE10225927A1 (de)	2003-12-24

Family

ID=29594383

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE10225927A Withdrawn DE10225927A1 (de)	2002-06-11	2002-06-11	Verfahren zur Herstellung von Butandiol durch kombinierte Gasphasen- und Flüssigphasensynthese

Country Status (8)

Country	Link
US (1)	US7169958B2 (zh)
EP (1)	EP1515935A1 (zh)
JP (1)	JP2005534658A (zh)
KR (1)	KR100898455B1 (zh)
CN (1)	CN1294110C (zh)
AU (1)	AU2003274707A1 (zh)
DE (1)	DE10225927A1 (zh)
WO (1)	WO2003104176A1 (zh)

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GB201318175D0 (en)	2013-10-14	2013-11-27	Johnson Matthey Davy Technologies Ltd	Process
CN106311255B (zh) *	2015-07-03	2019-12-24	中国石油化工股份有限公司	一种制备丁二醇用催化剂及其制备方法和应用
CN107537516B (zh) *	2016-06-28	2020-05-12	中国石油化工股份有限公司	用于制备仲丁醇的催化剂及其制备方法
CN112500418A (zh) *	2020-12-31	2021-03-16	山东中科新材料研究院有限公司	一种采用回路反应器合成1，8-二氮杂二环十一碳-7-烯的方法

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2002
- 2002-06-11 DE DE10225927A patent/DE10225927A1/de not_active Withdrawn
2003
- 2003-06-10 AU AU2003274707A patent/AU2003274707A1/en not_active Abandoned
- 2003-06-10 JP JP2004511246A patent/JP2005534658A/ja active Pending
- 2003-06-10 WO PCT/EP2003/006057 patent/WO2003104176A1/de not_active Ceased
- 2003-06-10 US US10/516,923 patent/US7169958B2/en not_active Expired - Fee Related
- 2003-06-10 CN CNB038133504A patent/CN1294110C/zh not_active Expired - Fee Related
- 2003-06-10 EP EP03740211A patent/EP1515935A1/de not_active Withdrawn
- 2003-06-10 KR KR1020047020104A patent/KR100898455B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CN1294110C (zh)	2007-01-10
EP1515935A1 (de)	2005-03-23
KR20050007606A (ko)	2005-01-19
JP2005534658A (ja)	2005-11-17
CN1659124A (zh)	2005-08-24
AU2003274707A1 (en)	2003-12-22
KR100898455B1 (ko)	2009-05-21
US7169958B2 (en)	2007-01-30
US20050267318A1 (en)	2005-12-01
WO2003104176A1 (de)	2003-12-18

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